Fungicidal N-sulphenylated hydantoins

Abstract

N-Sulphenylated hydantoins of the formula ##STR1## in which R 1 is trihalogenomethoxy or trihalogenomethylmercapto, R 2 is hydrogen, nitro or halogen, and R 3 and R 4 each independently is hydrogen or alkyl, or, together with the ring carbon atom at which they are located, form a five-membered or six-membered cycloalkyl radical, which possess fungicidal activity.

What is claimed is: 
     
       1. An N-sulphenylated hydantoin of the formula ##STR15## in which: R 1  is trihalogenomethoxy or trihalogenomethylmercapto, R 2  is hydrogen, nitro or halogen, and   R 3  and R 4  each independently is hydrogen or alkyl having 1 to 4 carbon atoms, or, together with the ring carbon atom at which they are located, form a five-membered or six-membered cycloalkyl radical.   
     
     
       2. A compound according to claim 1, in which:   R 1  is trichloromethoxy, trifluoromethoxy, trichloromethylmercapto, trifluoromethylmercapto, difluorochloromethoxy, fluorodichloromethoxy, difluorochloromethylmercapto or fluorodichloromethylmercapto,   R 2  is hydrogen, nitro or chlorine, and   R 3  and R 4  each independently is hydrogen or lower alkyl having 1 to 4 carbon atoms, or, together with the ring carbon atom at which they are located, form a cyclopentyl or cyclohexyl ring.   
     
     
       3. A compound according to claim 1, in which:   R 1  is trichloromethoxy, trifluoromethoxy, trichloromethylmercapto, trifluoromethylmercapto, difluorochloromethoxy, fluorodichloromethoxy, difluorochloromethylmercapto or fluorodichloromethylmercapto,   R 2  is hydrogen or chlorine, and   R 3  and R 4  each independently is hydrogen or lower alkyl having 1 to 3 carbon atoms, or, together with the ring carbon atom, form a cyclopentyl or cyclohexyl radical.   
     
     
       4. A compound according to claim 1, wherein such compound is 1-dichlorofluoromethylmercapto-3-(4-trifluoromethoxy-phenyl)-hydantoin of the formula ##STR16## 
     
     
       5. A compound according to claim 1, wherein such compound is 1-dichlorofluoromethylmercapto-3-(4-chlorodifluoromethoxy-phenyl)-hydantoin of the formula ##STR17## 
     
     
       6. A compound according to claim 1, wherein such compound is 1-dichlorofluoromethylmercapto-3-(4-trifluoromethylmercapto-phenyl)-hydantoin of the formula ##STR18## 
     
     
       7. A compound according to claim 1, wherein such compound is 1-dichlorofluoromethylmercapto-3-(3-chloro-4-trifluoromethoxy-phenyl)-hydantoin of the formula ##STR19## 
     
     
       8. A compound according to claim 1, wherein such compound is 1-dichlorofluoromethylmercapto-3-(3-chloro-4-chlorodifluoromethoxy-phenyl)-hydantoin of the formula ##STR20## 
     
     
       9. A fungicidal composition comprising a fungicidally effective amount of a compound according to claim 1 in admixture with a diluent. 
     
     
       10. A method of combating fungi which comprises administering to such fungi a fungicidally effective amount of a compound according to claim 1. 
     
     
       11. The method according to claim 10, wherein such compound is 1-dichlorofluoromethylmercapto-3-(4-trifluoromethoxy-phenyl)-hydantoin,   1-dichlorofluoromethylmercapto-3-(4-chlorodifluoromethoxy-phenyl)-hydantoin   1-dichlorofluoromethylmercapto-3-(4-trifluoromethylmercapto-phenyl)-hydantoin,   1-dichlorofluoromethylmercapto-3-(3-chloro-4-trifluoromethoxy-phenyl)-hydantoin, or   1-dichlorofluoromethylmercapto-3-(3-chloro-4-chlorodifluoromethoxy-phenyl)-hydantoin.